5 entrepreneurs and their biggest regrets

Five leading entrepreneurs tell us what they wish they'd done differently

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Updated: Sep 6, 2018 Published: Sep 7, 2011

Even the best entrepreneurs get it wrong from time to time, and no-one goes through their business career without making a decision they one day rue.

To demonstrate this inalienable truth, and provide some inspiration for our readers, we asked five of Britain’s most successful start-up entrepreneurs to tell us about the decision, or non-decision, they regret the most. Any start-up entrepreneur, in any field, should be able to relate to what they told us.

Don’t wait to start up

Paul Aitken set up Borro.com, a financial institution specialising in the sports and entertainment fields, in August 2008. The company now encompasses 45 employees, with a turnover of between £4 and £5m, and has plans in place for international expansion.

Borro is not Aitken’s first start-up; before founding the company he created a mobile phone connectivity company, and made a successful exit in 2005. But despite this rich entrepreneurial pedigree, Aitken wishes he’d chased his start-up dream even sooner.

“My view is that I should have taken the plunge of starting my own companies earlier than I did. Part of the reason was not having enough confidence to back myself. Likewise, at the time I was looking at doing start-ups in the early 90s, there was far less capital for start-ups than there is now.

“I had lots of ideas – in 1999, for example, I had everything fleshed out for a precursor to Facebook, but I never got it off the ground. I spent too much time planning and not enough time doing.

“I learned that, if you’ve got a good idea, you should back your judgement and go for it.”

Borrow as much as you can

Former glamour model Nikki Hesford decided to start her own business after graduating from university and experiencing frustration in the job market. Her company, Miss Fit UK, specialises in providing clothing for big busted women, and now boasts an annual turnover of around £350,000.

When Nikki started in 2008, she believes she should have taken greater risks early on.

“In the beginning, being a typical woman I just put a few thousand in here and there, and it took a good 18 months to get off the ground, largely because of me being risk-averse. With hindsight, rather than spending £1,000 a time on a credit card, I should have got £30,000 through a business loan. But the applications were so long and the banks were quite patronising – it was like ‘go home, Barbie doll’.”

Hesford believes that, if she’d gambled £30,000 up front, “we’d have had the success we’re having now at least one financial year earlier.

“Every single season I had only a skeleton selection, with only four or five products, so people would just say ‘we’ll come back next season’. People wanted to see 20 to 30 products, but I could only offer a handful. If I’d taken out a little more money, I could also have wholesaled – which I wish I’d done now.”

Test the business model

As founder of web development firm Moonfruit, Wendy Tan White came through the dotcom crash to create one of the UK’s most impressive technology companies. Moonfruit now turns over $4.5m a year, and over 3.5 million websites have been constructed using its ultra-simple design tools.

Today the company’s success is rooted in a realistic, scalable structure, designed to withstand all the turbulence and fluctuation of the technology industry. However, looking back at her business, Wendy believes she should have been much more pragmatic in the early days.

“I really regret the time around the NASDAQ crash in 2001 – if I’d known then what I do now I might have done things differently. We raised a lot of money in the first dotcom boom, like many companies, but we grew too quickly – we hadn’t found a business model that was scalable.

“A start-up should test the business model to the point where they know it’s scalable – customers pay for a service, and you sell it for less than you pay for it. We grew too fast before we had the scalable model in place. Before we were really clear about how we were going to make money for our product, before we even had a clear idea of what our product was, we had raised £6m. What that meant for us was that, when the NASDAQ cash and venture capital funding dried up, we didn’t know how to make ourselves scalable.”

Drawing on her experience, Tan White advises: “Don’t be scared to experiment, and don’t be scared to fail. When the NASDAQ crashed and we went down to me and Eric, we ground it out slowly, but we had no context – in the US, people expect you to try and fail, but in the UK there wasn’t context, and we felt we had to try and weather it out in our attic, and we stayed in that state too long. If I failed again today, I would not sit in that state for anywhere near as long.”

Listen to your audience

When Warren Bennett founded A Suit That Fits in June 2006, he had a clear vision: to create the world’s first online tailoring company, allowing customers to buy bespoke suits online rather than having to traipse to a shop. Unfortunately, the target audience didn’t share this vision.

“When we started we did a research poll and asked people how many would buy a suit online; 99% said they never would. That in itself should have told us we needed to open a studio (to complement the online business), but we didn’t do it until later.

“We did the market research ourselves, but we didn’t listen to it. We thought it was still a great idea, but we should have listened to what our customers were telling us.”

Bennett finally decided to open the studio in 2006, three months after launching the site. In reality, this decision did little harm to the business; A Suit That Fits now includes 33 stores nationwide, and the business turns over £1.2m. But Bennett believes he could have built the business even faster, had he adjusted his strategy to his market.

Think before you jump

Sahar Hashemi founded Coffee Republic with her brother Bobby in 1995. By the time she quit the business six years later, it had grown to a chain of 110 stores, turning of £30m and employing more than 2,000 people.

Many entrepreneurs would consider this an unqualified success; but Hashemi still harbours a lingering regret, because she could have stayed with the business and made it even better.

“I made the mistake of thinking that my time was over, and thinking a big company doesn’t require entrepreneurs. Ultimately I left because of conventional thinking, that you have a sell-by date as an entrepreneur, and the company doesn’t need you anymore. You have to start thinking of an exit.

“When we hired people who were quite senior I started to wonder if I was needed anymore. I felt I was being taken out of the equation. I thought I was leaving a good system in place, and we’d hired people who knew how to run big companies.”

However, things didn’t turn out as Hashemi had anticipated. In fact one of the senior employees “almost ran the company to the ground, because he lacked passion”. In the end, Bobby had to go back in to save the company.

With hindsight, Hashemi says, “I wish I’d never left. I was passionate about the brand, and on a store level, people missed me and Bobby being there”. She adds that all entrepreneurs must “realise how precious you are to the business, and make sure you are always able to have a say in the direction of the company”.